Réaction #684961

Équation de réaction

acetic acid

sodium hydroxide

m-anisaldehyde

nitromethane

→

title compound

Rendement 83.5%

1-(3-Methoxyphenyl)-2-nitro-1-ethanol

Rendement 83.5%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Autrehigher than 30° C
2. 2
   TempératureUpon cooling on ice
3. 3
   Autrethe resulting reaction mixture
4. 4
   Extractionwas extracted with ethyl acetate
5. 5
   LavageThe ethyl acetate layer was washed successively with water
6. 6
   Séchagea 5% aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by silica gel column chromatography

Mode opératoire

An aqueous sodium hydroxide solution (1.5 g of sodium hydroxide (37 mmol) was dissolved in 15 ml of water) was added dropwise to a solution of m-anisaldehyde (5.0 g, 37 mmol) and nitromethane (4.0 ml, 73 mmol) in methanol (50 ml) keeping the temperature of the solution at not higher than 30° C. The reaction mixture was then stirred at room temperature for 4 hours. Upon cooling on ice, an aqueous acetic acid solution (glacial acetic acid (37 mmol) was dissolved in 250 ml of water) was added, the resulting reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and a 5% aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (6.09 g).

Source